Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate → ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate

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Reaction Steps

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate (37) (105 mg, 0.16 mmol) in MeOH (4 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 25° C. under H2 (full H2 mode). The output was concentrated in vacuo, and a solid was collected by filtration after trituration with isohexane to afford ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate (UL1-102) (20 mg, 25%) as a yellow solid: m/z 462 (M+H)+ (ES+), 460 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.58 (s, 1H), 8.44 (s, 1H), 7.05-6.99 (m, 2H), 6.86-6.82 (m, 2H), 4.03-3.95 (m, 4H), 3.61-3.53 (m, 4H), 2.82 (br s, 6H), 2.45-2.34 (m, 6H), 1.93-1.81 (m, 2H), 0.98 (t, J=7.0 Hz, 3H).

Provenance & Evidence